Paisley, Renfrewshire born inside right Bob Dalrymple began his football career with local junior club Westmarch in 1899 before joining local Scottish Football League Second Division club Abercorn in 1900. In 1902, he moved to Edinburgh to play for First Division side Heart of Midlothian, making his debut that October against Hibernian, scoring in a 1-1 draw. He spent time with Kilbarchan on loan later in 1902 and went on to score two more goals that season, in a League game against Morton and a Scottish Cup tie at Ayr. Having helped the club reach the 1903 Scottish Cup Final, he played in a 1-1 draw against Rangers at Celtic Park on 11th April 1903 and the replay one week later, which also ended in a draw. Dalrymple received a runners-up medal after Hearts lost the second replay by two goals to nil on 25th April 1903, with 32,000 spectators in attendance. His 14 total games for Hearts included more cup ties than League games!
He then moved to England in the summer of 1903, joining Plymouth Argyle ahead of the club’s first season in professional football. He made his Southern League debut in a 1-0 win at West Ham United on 1st September 1903, and scored his first goal at the end of the month as the club defeated Portsmouth by three goals to one. A versatile player, Dalrymple scored the club’s first goal in the FA Cup and scored a second later in the game as Argyle defeated Whiteheads by seven goals to nil in the first qualifying round. He finished the season with 17 goals scored in all competitions, having made 43 appearances. The following season, he was among the goals in the FA Cup again, earning Argyle a 1-1 draw at Newcastle United in the first round on 4th February 1905. He scored a further 12 goals in league competition, including a brace in a 4-1 win against Southampton, and won his first major title at the end of the season as the club were crowned Western Football League champions.
He moved back to Scotland in the summer of 1905, having scored 30 goals in 92 appearances for Plymouth Argyle, to sign for Glasgow Rangers. He made his debut on 19th August 1905 as they defeated Kilmarnock by three goals to two at Ibrox. He scored his first goal in the return match at Kilmarnock on 6th January 1906, which Rangers won 3-1, and scored a hat-trick two weeks later in a 4-0 home win against Port Glasgow Athletic. In the Scottish Cup, Dalrymple scored a brace in victories against Arthurlie and Aberdeen, before Rangers were eliminated by Port Glasgow Athletic in the quarter finals. He made 15 appearances in his one season with the club, scoring 8 goals.
Dalrymple returned to England in 1906, where he spent a season back in the Southern League with Portsmouth. The following year, he joined Fulham ahead of their first season in The Football League.. He scored 43 goals in 108 appearances over the next three years, playing in their inaugural League fixture against Hull City in September 1907, a season in which he top scored with 22 goals including hat-tricks against Gainsborough Trinity and Clapton Orient, and helped the club reach the FA Cup semi final in 1908, where they were beaten 6-0 by Newcastle United at Anfield.
In January 1911 he moved to Second Division club Clapton Orient and spent the next nine years there, playing both sides of the First World War, during which he served as a Sergeant in the 17th (Service) Battalion of The Duke of Cambridge’s Own (Middlesex) Regiment, better known as The Footballers’ Battalion, scoring 38 goals in 143 appearances for Orient. But he only played 7 matches once peacetime football resumed, his last coming at Bury in November 1919, before he finished his career back in the Southern League with Welsh side Ton Pentre signing for them in 1920, playing for them until his eventual retirement.